Month: December 2020

Synthetic Route of 13745-86-3, These common heterocyclic compound, 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 1 Preparation of 1 l-piperazin-l-yldibenzor&,/iri,4~lthiazepineInto a 1000 mL round-bottom flask equipped with a magnetic stirring bar and reflux condenser with a nitrogen inlet was charged with 25.0 grams (g) (0.110 mole) of dibenzo[b,fj[l,4]thiazepine-l l(10-H)-one (made by the method disclosed by J. Schmutz et al. HeIv. Chim. Acta., 48: 336 (1965)), as a dry solid, followed by 310 mL POCl3 and 3 mL of N,N-dimethylaniline. The reaction mixture was heated at reflux (106 degrees C) for 6 hours giving a clear orange solution. The reaction was then cooled to room temperature, and POCl3 removed on the rotary evaporator leaving an orange oil. This residue was partitioned between ice -water (500 mL) and ethyl acetate (800 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (3 X 200 mL). The combined ethyl acetate extracts were dried over MgSO4 , filtered, and then stripped down on the rotary evaporator, leaving the crude imino chloride as a light yellow solid (26.26g, 97% yield). The structure was confirmed by NMR and Mass Spectrum (300 MHz, CDCl3; ES+, M+l = 246.7). Crude imino chloride (27.35 g, 0.111 mole) was added to 1000 mL o-xylene in a 2000 mL round-bottom flask equipped with a magnetic stir bar and a reflux condenser with nitrogen inlet. To this solution was added commercially available piperazine (47.95g, 0.557 mole) in one portion as a dry solid at room temperature. The mixture was stirred until nearly all the piperazine dissolved. EPO Then the reaction mixture was heated at reflux (142 degrees C) for 40 hours (out of convenience). The reaction was then allowed to cool to room temperature, and an aliquot was partitioned between IN NaOH / CH2Cl2. The organic phase was checked by TLC (silica gel, CH2Cl2 / Methanol 90:10, iodoplatinate visualized) and showed clean conversion to one major product (Rf = 0.45). A drop of the reaction solution was diluted with CH3CN to prepare a sample for LC / MS analysis, which confirmed the presence of the desired product (M+l = 296.4). The reaction mixture was stripped down on the rotary evaporator under high vacuum to remove the xylene. The residue was partitioned between IN NaOH (400 mL) and CH2Cl2 (200 mL). The layers were separated, and the aqueous phase further extracted with CH2Cl2 (3 X 200 mL). The combined CH2Cl2 extracts were washed with brine (200 mL), then dried over MgSO4, filtered, and stripped down on the rotary evaporator to give the crude title compound as a yellow gum (35.3 g). The crude free base was purified by flash column chromatography over silica gel (600 g) eluting with a gradient of 0 to 20% Methanol in CH2Cl2. Fractions containing the pure desired product were combined and stripped down on the rotary evaporator, to afford the purified free base as a light yellow foam (25.67g, 78% yield).

The synthetic route of 13745-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/73360; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 873-38-1, name is 2-Bromo-4-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Bromo-4-chloroaniline

2-Bromo-4-chloroaniline (1.0 eq) was dissolved in CH2Cl2(0.25M), then triethylamine and triflouroacetyl anhydride (1.1 eq each) were added. The resulting mixture was stirred at room temperature for 1 hour. Solvent was then stripped-off from the reaction mixture, and the residue was purified by flash chromatography with dichloromethane as eluent to give the described product in 97% yield. m/z(M-H) -300.0.

According to the analysis of related databases, 873-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2008/9485; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2845-89-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2845-89-8 name is 1-Chloro-3-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Pd(OAc)2 or Pd2(dba)3/2-Catalyzed Amination of Aryl chlorides (Table 5).General Procedure: An oven-dried Schlenk flask equipped with a magnetic stirring bar was charged with Pd(OAc)2 or Pd2(dba)3 (x mol %, see Table 5) and NaO-t-Bu (1.5 mmol) or Cs2CO3 (1.5 mmol). Amine (1.2 mmol) and aryl chloride (1.0 mmol) were also added at this time if they were solids. The flask was capped with a rubber septum, evacuated and then flushed with argon. This cycle was repeated three times. Ligand 2 (2x mol %, see Table 5) was then added via syringe from a stock solution. Aryl chloride (if a liquid, 1.0 mmol), amine (if a liquid, 1.2 mmol) and toluene (3 mL) were then successively added by syringe. The reaction mixture was heated at 110 C. until the starting material had been completely consumed as judged by TLC (24 hours). The mixture was cooled to room temperature, adsorbed onto silica gel and then purified by column chromatography (hexanes/ethyl acetate as eluent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Chloro-3-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; Iowa State University Research Foundation, Inc.; US7385058; (2008); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 108649-59-8,Some common heterocyclic compound, 108649-59-8, name is 1-(2-Bromoethyl)-2,4-dichlorobenzene, molecular formula is C8H7BrCl2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step i: Synthesis of 2-bromo-5-(2,4-dichlorophenethyl)-4,5,6 ,7-tetrahvdrothiazolo[5,4-clpyridine A mixture of l-(2-bromoethyl)-2,4-dichlorobenzene (0.1 g, 0.000393 mol) and 2-bromo-4,5,6,7- tetrahydrothiazolo[5,4-c]pyridine(0.103 g, 0.000472 mol) in DMF (2 mL) was cooled to 0 – 5 C, and added NaH (0.014 g, 0.00059 mol). The RM was then warmed to 60 C for 6 h. The RM was cooled to RT, quenched with water, extracted into ethyl acetate and organic portion was washed with water, dried over sodium sulphate, concentrated to get the titled compound (0.06g, 38.2%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Bromoethyl)-2,4-dichlorobenzene, its application will become more common.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; KOTRABASAIAH UJJINAMATADA, Ravi; HOSAHALLI, Subramanya; BEJUGAM, Mallesham; WO2015/101928; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 14495-51-3, The chemical industry reduces the impact on the environment during synthesis 14495-51-3, name is 2-Bromo-5-chlorotoluene, I believe this compound will play a more active role in future production and life.

Compound 3 (20.7 mmol) was dissolved in CH2Cl2 (150 mL) and cooled to 0 C. with ice bath. To this solution under nitrogen were added in sequence N,N-di-isopropyl ethyl amine (5.4 mL, 31.02 mmol, 1.5 eq) and chloromethyl methyl ether (2 mL, 25.85 mmol, 1.25 eq). The reaction mixture was stirred overnight at room temperature and washed with NaHCO3-saturated water and then NaCl-saturated water. The residue after rotary evaporation was purified by flash column chromatography over silica gel to give 17.6 mmol of 4.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Bromo-5-chlorotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Baker, Stephen J.; Sanders, Virginia; Akama, Tsutomu; Bellinger-Kawahara, Carolyn; Freund, Yvonne; Maples, Kirk R.; Plattner, Jacob J.; Zhang, Yong-Kang; Zhou, Huchen; Hernandez, Vincent S.; US2007/293457; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 367-21-5,Some common heterocyclic compound, 367-21-5, name is 3-Chloro-4-fluoroaniline, molecular formula is C6H5ClFN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 3-chloro-4-fluoroaniline (5.82 g, 0.04 mol) in CH2Cl2(150 mL), N-bromosuccinimide (7.12 g, 0.04 mol) was added in portions at 0C under stirring. Upon completion of the addition, the resultant was stirred for 30 minutes and filtered. The filtrate was concentrated and purified by silica gel column chromatography to give 2-bromo-5-chloro-4-fluoroaniline (6.16 g, 69% yield). 1H-NMR (400 MHz, CDCl3):delta = 7.234 (d, J = 8.4 Hz, 1H), 6.788 (d, J = 6.4 Hz, 1H), 3.982 (br, 2H). MS m/z [ESI]: 225.9 [M+1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-4-fluoroaniline, its application will become more common.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XIAO, Dengming; XU, Xinhe; LIU, Xijie; HU, Yuandong; YU, Honghao; LIU, Zhihua; PENG, Yong; SUN, Yinghui; LUO, Hong; KONG, Fansheng; HAN, Yongxin; SUN, Jian; EP2952510; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 367-22-6, name is 4-Chloro-3-fluoroaniline, A new synthetic method of this compound is introduced below., Safety of 4-Chloro-3-fluoroaniline

Into a 500-mL round-bottom flask, was placed 4-chloro-3-fluorobenzenamine (5.08 g, 34.9 mmol), ACN (200 mL) and NBS (18.69 g, 105.0 mmol). The resulting solution was stirred for 12 h at RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:200 to 1:100). This resulted in 9.7 g (92%) of the title compound as a light yellow solid. MS-ESI: 303.8, 305.8, 301.8 (M+1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; IFM THERAPEUTICS, INC; GLICK, Gary; GHOSH, Shomir; ROUSH, William R.; (328 pag.)WO2017/184624; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 13918-92-8, A common heterocyclic compound, 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(1) 5-Bromo-3-amino-2-chloropyridine (0.10 g, 0.48 mmol), pyridine (0.057 g, 0.72 mmol), and dissolved in dichloromethane (0.77 mL) to prepare reaction solution 1. 2,4-difluorophenylsulfonyl chloride (0.12 g, 0.58 mmol) was used to prepare reaction solution 2. The flow rate (0.5 mL / min) set by the intelligent numerical control sampler was simultaneously introduced into the first via a 500 mum picker tube. Mix in a three-way mixer (ambient temperature 0 C), then flow out under its own pressure, enter a 500 mum inside diameter tube with a set temperature control (25 C), and set the residence time t1 (0.5min). the sulfonamide complete reaction, followed by after-pressure valve to obtain a first effluent;

The synthetic route of 13918-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; Zhuhai Fudan Chuangxin Institute; Ling Yun; Zhou Yaming; Jia Yu; Deng Mingli; Liu Xiaofeng; Yang Yongtai; Chen Zhenxia; (30 pag.)CN110498798; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 51572-93-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 51572-93-1, name is O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of substituted O-benzylhydroxylamine hydrochloride (1 equiv), TEA (1 equiv) and substituted salicylaldehyde (1 equiv) was dissolved in absolute ethanol and stirred for 0.5 h. The reaction was monitored by TLC. The precipitate was filtered and recrystallized from ethanol to gain salicylaldoxime (compounds 1g-20g).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Ting-Ting; Lu, Xiang; Yang, Xian-Hui; Wang, Li-Ming; Li, Xi; Wang, Zhong-Chang; Gong, Hai-Bin; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 10; (2012); p. 3233 – 3241;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2533-69-9, Product Details of 2533-69-9

A solution of 5,6-difluorobenzene-1,2-diamine (1.76 g, 12.2 mmol) in acetic acid (70 ml) was treated with methyl-2,2,2-trichloroacetimidate (1.5 ml, 12.2 mmol) and the resulting solution left to stir at room temperature for 16 hours. The solvent was removed in vacuo and the residue was dissolved in methanol (100 ml) and heated to reflux for 4 hours. The solvent was removed in vacuo and the residue partitioned between saturated aqueous sodium bicarbonate (100 ml) and ethyl actetae (100 ml). The organic phase was separated, dried (sodium sulphate) and reduced in vacuo. Purification by flash column chromatography on silica gel eluting with pentane:ethyl acetate (90:10 changing to 50:50, by volume) gave the title compound as a yellow solid (963 mg).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Lane, Charlotte Alice Louise; Price, David Anthony; US2006/111416; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics